Troglitazone → 3-Ethyl-5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4dione

HRID 1030383Notes

Reaction equation

HRID 1030383 reaction equation
[OH:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:38](I)[CH3:39]>CC(C)=O>[CH2:38]([N:24]1[C:23](=[O:28])[CH:22]([CH2:21][C:20]2[CH:29]=[CH:30][C:17]([O:16][CH2:15][C:7]3([CH3:14])[CH2:6][CH2:5][C:4]4[C:9](=[C:10]([CH3:13])[C:11]([CH3:12])=[C:2]([OH:1])[C:3]=4[CH3:31])[O:8]3)=[CH:18][CH:19]=2)[S:26][C:25]1=[O:27])[CH3:39]

Participants

5

Reactant 3

HCID 5591TroglitazoneHCID 6340IodoethaneHCID 11430Potassium Carbonate

Product 1

HCID 198222853-Ethyl-5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the procedure described in Example 44, 0.58 g of 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione [prepared as described in Example 27(b)], 0.27 g of anhydrous potassium carbonate, 0.6 g of ethyl iodide and 5 ml of acetone gave the title compound.

Sources & evidence

ORD record
ord-03d802d68a714e709098d5cfe9006c6d
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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